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My wife is starting a residency in Asia in ~13 months, and I am planning to move with her. It feels like the opportunity of a lifetime, and I've already started learning the language. We currently live in the US, the residency is only 3 months long, and we'll move back to the US when she finishes. But I'm worried how to make this actually happen with my career, and how to bring it up with my employer.

I'm optimistic that my current employer will let me work in Asia for 3 months. My current tenure is 4 years, I have a great reputation, and the company is 100% remote (but based in the US). I feel independent enough that I can work from an Asia timezone. But when and how should I bring this up with my manager? Are there any resources or framework for making this kind of decision?

I'm thinking about presenting it as less of a choice, and more of a family situation, but I'd love to hear other opinions. It's a startup, so there is no official policy, other than a "personal, non-medical, unpaid leave". I'd be willing to take that if possible. I'm thinking about bringing this up to my manager ~6 months before I plan to leave.

Also, I've been applying to new jobs. While I'm happy at my current job, I'm eager to try something new, perhaps at a more prestigious company. But I'm not sure how moving to Asia will affect a new job. It feels like a stretch to start a new job, build enough rapport in a few months, then request working from Asia for 3 months. I have ~9 years of experience, a regular OSS contributor, so I feel confident in ramping up quickly. Maybe it can work? Or maybe I can find a company that will agree up front about my relocation plans?

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    Ask your manager how you would request this. The answer will vary from company to company, and potentially between management chains within a company.
    – keshlam
    Commented Jul 30, 2023 at 3:29
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    Visa and tax requirements vary by country; 90 days is usually OK to visit and work remotely without a visa but often not more than that.
    – mxyzplk
    Commented Jul 30, 2023 at 5:28
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    even if a work visa isn't a problem, working abroad has tax complications that might make it infeasible for your employer if you're salary rather than an independent contractor. Commented Jul 30, 2023 at 5:53
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    What are you going to do if, when you present this as a fait accompli to your employer, they say "no. Today's your last day. Pack your things and leave the office immediately"? That's the risk of playing hardball, particularly in a jurisdiction with essentially zero employee rights. Commented Jul 30, 2023 at 6:21
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    Ask your manager this question to explore what options the company may give you. But, don't make your question look like a demand that your manager must follow. The sooner you ask, the better it is as it gives you more time to explore your options. Commented Jul 30, 2023 at 18:29

5 Answers 5

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I'm thinking about presenting it as less of a choice, and more of a family situation, but I'd love to hear other opinions. It's a startup, so there is no official policy, other than a "personal, non-medical, unpaid leave". I'd be willing to take that if possible. I'm thinking about bringing this up to my manager ~6 months before I plan to leave.

If you have a good rapport with your manager, it makes complete sense to start out with an informal conversation. Explain what you plan to do, and ask how you can make it work.

Shoot for a remote work situation, if that is your preference, and fall back to an unpaid 3 month leave only if necessary.

Startups tend to be more informal and flexible. The ones I worked for often made this work for folks going to India for a few months - although we did have a tax nexus there.

Also, I've been applying to new jobs. While I'm happy at my current job, I'm eager to try something new, perhaps at a more prestigious company. But I'm not sure how moving to Asia will affect a new job. It feels like a stretch to start a new job, build enough rapport in a few months, then request working from Asia for 3 months. I have ~9 years of experience, a regular OSS contributor, so I feel confident in ramping up quickly. Maybe it can work? Or maybe I can find a company that will agree up front about my relocation plans?

You can always try to land a new job before the 3 month trip.

Be up front with potential employers about your need for the leave. Remote work might be a stretch, or it might not. And the 3 month unpaid leave might also be a deal breaker. It probably depends on the company, your role, and your desirability as an employee.

Worse comes to worst, you drop the job search and pick it back up when you return.

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You should begin conversations with your manager and HR department sooner rather than later. Even if they are inclined to let you work remotely, there may be external factors which will stand in the way.

Both you and the company need to research any external impacts, including:

  • Tax laws as they impact you and your employer
  • A work visa may be required
  • depending on the industry and the nature of your work, there may be limits on what you can/should work on.

Any of these could unfortunately be a blocker regardless of your company's initial level of support for your idea. The more time you give them to work on this, the better your chances.

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You should consider not traveling with your wife for the entire time, and working normally in the US as much as possible.

The first problem is that your timelines are all very awkward. You can't even know if you'll be working for your current company in 13 months, let alone what any job search will result in. It's going to be awkward if you start a new job in six months, and tell your new employer "I'm going to work for you for six months, then take 3 months of vacation."

Second, as others have alluded, the tax and visa issues are going to be very difficult, especially for a small company. It's one thing if you are going to India, and your company has an office there already. It's quite another if you'll be in Laos for three months.

Finally, even if you pull that off, the timezone issues, and your general desire to be a tourist there instead of work (very understandable) will be awkward.

I think you have two good options:

  1. Quit your job, and travel with your wife as a pure tourist. You are thinking of leaving anyway, so just time your job transition to match this trip, and find a new one when you return.
  2. Go with her for 2-4 weeks, instead of the entire time, and work normally otherwise. I understand that a 2 month separation can be difficult, but it will be temporary and end sooner than you expect.
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Good answer already on the time difference issues.

I'm thinking about presenting it as less of a choice, and more of a family situation

This is what I would do. It's best presented as a minor issue you're just informing them about out of courtesy. This leaves the ball in the employers hands and you can decide what to do if their stance is problematic.

Sometimes it pays to just assume everyone will do what you want both at work and in life and go ahead with your plans. Judgement call on this of course. Once you start asking for permission things can get complicated fast. Most people will take the path of least resistance unless there is an over-riding reason not to.

Every country I'm familiar with you can work remotely while on a tourist visa for the duration of your visa. You don't have to inform anyone. Things only get complicated if you enter into a local contract or involve local companies in your business.

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You're an autonomous, free-willed human being. Your life belongs to you. Your career belongs to you.

I get it, you value your position with the company, you want to be professional, and you want to give them as much notice as possible, so go to your manager now.

"Hey boss, I'm going to be making a life change. How will this impact my position here? Do we need to make any adjustments to my position, work hours, etc.?"

If you're looking for a new job, then address this up front. Make this a condition of your employment.

"I'll be moving to Asia for 3 months during the time period of X through Y."

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